Reaction equation
[CH2:1]([N:5]([CH2:17][CH2:18][CH2:19][CH3:20])[C:6](=O)[N:7]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29]>C(#N)C>[CH2:1]([N:5]([CH2:17][CH2:18][CH2:19][CH3:20])[C:6](=[N:30][CH2:26][CH2:27][CH2:28][CH3:29])[N:7]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 5.69 grams (20 mmol) of tetra-n-butylurea, 3.22 grams (21 mmol) of phosphorus oxychloride and 15 ml of acetonitrile was heated at 75° C. in a nitrogen atmosphere for one hour. The mixture was then cooled to 0° C. and 3.36 grams (46 mmol) of n-butylamine was added over 15 minutes with stirring. The mixture was warmed to 60° C. for one hour and again cooled to 0° C., quenched with 5 ml of 25% (by weight) aqueous sodium hydroxide solution and extracted with diethylether. The ether extracts were dried over sodium sulphate, filtered and stripped to give a pale yellow oil of penta-n-butylguanidine.
Workup
- temperatureThe mixture was then cooled to 0° C.
- temperatureThe mixture was warmed to 60° C. for one hour
- temperatureagain cooled to 0° C.
- customquenched with 5 ml of 25% (by weight) aqueous sodium hydroxide solution
- extractionextracted with diethylether
- dry with materialThe ether extracts were dried over sodium sulphate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-2146dd7589814ff595e4d32eb410833d
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303201B2
Linked notes
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